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Tumor inhibiting [1,2-bis(fluorophenylethylenediamine]platinum-(II) complexes. Part I: synthesis

Authors
Journal
European Journal of Medicinal Chemistry
0223-5234
Publisher
Elsevier
Publication Date
Volume
24
Issue
4
Identifiers
DOI: 10.1016/0223-5234(89)90076-7
Keywords
  • Diastereomeric 1
  • 2-Bis(2-
  • 3- And 4-Fluorophenyl)Ethylenediamines
  • Diaza-Cope-Rearrangement
  • [1
  • 2-Bis(2-
  • 3- And 4-Fluorophenyl)Ethylenediamine] Dihaloplatinum(Ii) Complexes
  • Diaqua[1
  • 2-Bis(2-
  • 3- And 4-Fluorophenyl)Ethylenediamine] Platinum(Ii) Salts
  • P388D1Leukemia Cell Line
  • Structure Activity—Relationship

Abstract

Abstract The synthesis of the diastereomeric 1,2-bis(2-,3- and 4-fluorophenyl)ethylenediamines 4–6, 10–12 from meso-1,2-bis(2-hydroxyphenyl)ethylenediamine and 2-, 3- and 4-fluorobenzaldehyde by a diaza-Cope-rearrangement and their conversion into the [1,2-bis(2-, 3- and 4-fluorophenyl)ethylenediamine]dihaloplatinum (II) complexes (Hal = Cl, 13–18; Hal = I, 19–24) with K 2PtHal 4 is described. From the diiodoplatinum(II) complexes ( 19–24) the better water soluble diaqua[1,2-bis(2-, 3- and 4-fluorophenyl)ethylenediamine]platinum(II) sulfates ( 25–30) and [1,2-bis(4-fluorophenyl)ethylenediamine]dinitratoplatinum (II) complexes ( 31 and 32) are obtained by reacting with Ag 2SO 4 or AgNO 3. On the P388D 1 leukemia cell line the racemic platinum (II) complexes are more active than their meso-analogues and equiactive with cis-platin. The position of the fluorine atom and the kind of the leaving group do not influence the activity.

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